Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H17N3S.2ClH |
| Molecular Weight | 284.249 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.CCCN[C@@H]1CCC2=C(C1)SC(N)=N2
InChI
InChIKey=QMNWXHSYPXQFSK-XCUBXKJBSA-N
InChI=1S/C10H17N3S.2ClH/c1-2-5-12-7-3-4-8-9(6-7)14-10(11)13-8;;/h7,12H,2-6H2,1H3,(H2,11,13);2*1H/t7-;;/m1../s1
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C10H17N3S |
| Molecular Weight | 211.327 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Dexpramipexole (also known as KNS-760704/R-pramipexole) was originally developed by University of Virginia researchers to treat Amyotrophic Lateral Sclerosis and then was licensed to global biotechnology company Biogen Idec for further development. However, on phase III clinical trial the study of this drug was discontinued. Biogen said the drug neither slowed the loss of muscle function nor prolonged the lives of patients with ALS, often called Lou Gehrig’s disease. Nor did it show any efficacy in secondary endpoints of the clinical trial, or work in any sub-group of patients—about a big a failure as a company could have a Phase III trial. In addition, was discovered, that dexpramipexole was able to bind to beta-subunit of the mitochondrial F1/FO ATP synthase complex and increased its activity, thus reduced ischemic brain injury. These findings, together with the excellent brain penetration and favorable safety profile in humans, make dexpramipexole a drug with realistic translational potential for the treatment of stroke.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
479 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20959524 |
150 mg 2 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DEXPRAMIPEXOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
781 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20959524 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXPRAMIPEXOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3749 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20959524 |
150 mg 2 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DEXPRAMIPEXOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8624 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20959524 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXPRAMIPEXOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20959524 |
150 mg 2 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DEXPRAMIPEXOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
6.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20959524 |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
DEXPRAMIPEXOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Fall, Muscular weakness... Other AEs: Fall (25%) Sources: Muscular weakness (16%) Constipation (25%) Salivary hypersecretion (11%) Depression (11%) Dyspnea (14%) Dysarthria (11%) Dysphagia (9%) Headache (14%) Dry mouth (16%) Oedema peripheral (2%) Upper respiratory tract infection (7%) Anxiety (11%) Sinusitis (11%) Cough (11%) Insomnia (14%) Muscle spasticity (2%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Anxiety | 11% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Cough | 11% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Depression | 11% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Dysarthria | 11% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Salivary hypersecretion | 11% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Sinusitis | 11% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Dyspnea | 14% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Headache | 14% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Insomnia | 14% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Dry mouth | 16% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Muscular weakness | 16% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Muscle spasticity | 2% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Oedema peripheral | 2% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Constipation | 25% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Fall | 25% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Upper respiratory tract infection | 7% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
| Dysphagia | 9% | 150 mg 2 times / day multiple, oral Highest studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pramipexole v. levodopa as initial treatment for Parkinson's disease: a randomized clinical-economic trial. | 2004-09-11 |
|
| The activity of pramipexole in the mouse forced swim test is mediated by D2 rather than D3 receptors. | 2004-09 |
|
| The effects of dopamine D3 agonists and antagonists in a nonhuman primate model of tardive dyskinesia. | 2004-08 |
|
| Restless legs symptoms in a patient with above knee amputations: a case of phantom restless legs. | 2004-07-15 |
|
| Pramipexole for bipolar II depression: a placebo-controlled proof of concept study. | 2004-07-01 |
|
| Pramipexole vs levodopa as initial treatment for Parkinson disease: a 4-year randomized controlled trial. | 2004-07 |
|
| [Pharmacological profiles and clinical effects of antiparkinsonian agent, pramipexole]. | 2004-06 |
|
| Furfuryl ethyl ether: important aging flavor and a new marker for the storage conditions of beer. | 2004-03-24 |
|
| Pramipexole for the treatment of uremic restless legs in patients undergoing hemodialysis. | 2004-03-09 |
|
| Conversion from dopamine agonists to pramipexole. An open-label trial in 227 patients with advanced Parkinson's disease. | 2004-03 |
|
| Preliminary randomized, double-blind, placebo-controlled trial of pramipexole added to mood stabilizers for treatment-resistant bipolar depression. | 2004-03 |
|
| Slowing Parkinson's disease progression: recent dopamine agonist trials. | 2004-01-27 |
|
| Slowing Parkinson's disease progression: recent dopamine agonist trials. | 2004-01-27 |
|
| Quality of life in early Parkinson's disease: impact of dyskinesias and motor fluctuations. | 2004-01 |
|
| Predictors of impaired daytime sleep and wakefulness in patients with Parkinson disease treated with older (ergot) vs newer (nonergot) dopamine agonists. | 2004-01 |
|
| Augmentation and tolerance with long-term pramipexole treatment of restless legs syndrome (RLS). | 2004-01 |
|
| Low-dose pramipexole in the management of restless legs syndrome. An open label trial. | 2004 |
|
| [A comparative study of efficacy of dopamine receptors agonists and catechol-O-methyltransferase in the treatment of late stages of Parkinson's disease]. | 2004 |
|
| Efficacy, safety, and tolerability of pramipexole in untreated and levodopa-treated patients with Parkinson's disease. | 2003-12-15 |
|
| Fibromyalgia and pramipexole: promise and precaution. | 2003-12 |
|
| Pramipexole in Restless Legs syndrome. Evaluation by suggested immobilization test. | 2003-12 |
|
| The effects of pramipexole in REM sleep behavior disorder. | 2003-11-25 |
|
| Pramipexole in the management of restless legs syndrome: an extended study. | 2003-11-01 |
|
| Randomized, double-blind, 3-month parallel study of the effects of pramipexole, pergolide, and placebo on Parkinsonian tremor. | 2003-11 |
|
| Neuroprotective effects of the novel D3/D2 receptor agonist and antiparkinson agent, S32504, in vitro against 1-methyl-4-phenylpyridinium (MPP+) and in vivo against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP): a comparison to ropinirole. | 2003-11 |
|
| Oral anticoagulation for ECG tremor artefact simulating atrial fibrillation. | 2003-10 |
|
| Randomized, double-blind study of pramipexole with placebo and bromocriptine in advanced Parkinson's disease. | 2003-10 |
|
| Clinical strategies to prevent and delay motor complications. | 2003-09-23 |
|
| Treatment effects on nigrostriatal projection integrity in partial 6-OHDA lesions: comparison of L-DOPA and pramipexole. | 2003-09 |
|
| Pramipexole inhibits MPTP toxicity in mice by dopamine D3 receptor dependent and independent mechanisms. | 2003-08-15 |
|
| Pathological gambling associated with dopamine agonist therapy in Parkinson's disease. | 2003-08-12 |
|
| Pramipexole increases vesicular dopamine uptake: implications for treatment of Parkinson's neurodegeneration. | 2003-08-08 |
|
| Pramipexole and pergolide in the treatment of depression in Parkinson's disease: a national multicentre prospective randomized study. | 2003-07 |
|
| REAL and CALM: what have we learned? | 2003-07 |
|
| Reduction of oxidative stress in amyotrophic lateral sclerosis following pramipexole treatment. | 2003-06 |
|
| [Treatment of restless legs syndrome in uremic patients undergoing dialysis with pramipexole: preliminary results]. | 2003-06 |
|
| The use of dopamine enhancing medications with children in low response states following brain injury. | 2003-06 |
|
| The initial drug treatment of older patients with Parkinson's disease - consider an agonist, but don't demonise dopa. | 2003-05 |
|
| Pramipexole in Parkinson's disease. A short-term study using the combined levodopa-dopamine agonist test. | 2003-04-05 |
|
| Pramipexole in comparison to l-dopa: a neuropsychological study. | 2003-04 |
|
| [(123)I]beta-CIT SPECT is a useful method for monitoring dopaminergic degeneration in early stage Parkinson's disease. | 2003-03 |
|
| Double-blind, single-dose, cross-over study of the effects of pramipexole, pergolide, and placebo on rest tremor and UPDRS part III in Parkinson's disease. | 2003-02 |
|
| Multiple blood donations associated with iron deficiency in patients with restless legs syndrome. | 2003-01 |
|
| Loss of color vision during long-term treatment with pramipexole. | 2003-01 |
|
| Pramipexole in routine clinical practice: a prospective observational trial in Parkinson's disease. | 2003 |
|
| Cabergoline, pramipexole and ropinirole used as monotherapy in early Parkinson's disease: an evidence-based comparison. | 2003 |
|
| Comparison of the risk of adverse events with pramipexole and ropinirole in patients with Parkinson's disease: a meta-analysis. | 2003 |
|
| Neuroprotection in idiopathic Parkinson's disease. | 2002-10 |
|
| Combination of two different dopamine agonists in the management of Parkinson's disease. | 2002-09 |
|
| Pergolide-associated 'sleep attacks' in a patient with restless legs syndrome. | 2002-05 |
Patents
Sample Use Guides
It was found that dexpramipexole (DEX) binds to the oligomycin sensitivity–conferring protein (OSCP) and b-subunits of the F1/FO ATP synthase, suggesting that it may indirectly inhibit the c-subunit (mPTP) pore by producing a conformational change in complex V that places F1 over the pore, inhibiting its conductance. The human open reading frame constructs for α, β, b, c, δ, d, ε, γ, and oligomycin sensitivity–conferring protein (OSCP) ATP synthase subunits were used. 293T cells were transfected with the above constructs. On day 3 post-transfection, the cells were lysed. The proteins were eluted from a portion of the samples, and the presence of the proteins on the beads was verified by immunoblot analysis, using mouse anti-Myc antibodies. The protein-bound beads were incubated in the presence of [14C]DEX (range of concentration was: 1-10 uM).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:51:54 GMT 2025
by
admin
on
Mon Mar 31 19:51:54 GMT 2025
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| Record UNII |
I9038PKO43
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID20920539
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51052075
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300000044498
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104632-27-1
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1553815
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SOLVATE->ANHYDROUS | |||
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |